‘We Need To Talk’: As Hard To Say As It Is To Hear

Being on the receiving end of a conversation that starts with those words is tough. But I’d say being on the other side of it can be just as challenging – sometimes maybe even more so.

As CEO of several startups over the years, I’ve had to initiate many difficult conversations. And while I’ll probably never look forward to them, I’ve learned that there are things I can do to handle them better and in ways that end up benefiting everyone involved.

I’d like to share some of those lessons with you in hopes that they’ll help you achieve the best possible outcome the next time you have to give an employee a less-than-positive review, get your team onboard with a major change in direction or share disappointing financial results with investors.

Think positive.

I’m generally a very positive person, and I’ve come to believe that particular quality – perhaps more than anything else – has really helped conversations end well that could just as easily have gone off the rails. Look at the examples above; each is enough to make any leader’s palms sweat. But each is also anopportunity for a positive outcome: an employee who’s motivated to do better after a poor review, a team that can get behind a vision even as it’s changing, investors who maintain their confidence in your leadership despite a challenging quarter. The first step in taking advantage of those opportunities is recognizing them and keeping them foremost in your mind as the conversation unfolds.

Be prepared.

Positive thinking can take you a long way, but preparation can take you even further. Don’t just promise better financial performance; bring forecasts and projections that show how to turn it around. Or couple a poor performance review with some specific suggestions for improvement. Keep in mind, though, that when I say “be prepared,” I’m not suggesting you try to create a script you can follow for your conversation. That rarely works out well, because it doesn’t take into account the need to retain flexibility and allow for how the other party or parties may respond to whatever you’re putting out there. I’m just saying that coming prepared with facts and information to back up your positive attitude increases your credibility and gives people something to work with in the aftermath of the conversation.

Be direct.

Nobody likes having to say something that may be difficult to hear, but if that’s what you must do, take a cue from Nike and just do it. Once you’ve said “we need to talk” – in whatever words you use to say that – it’s not fair to make the other person wait for the news. Don’t put it off; have the conversation as soon as possible. Once you do sit down to talk, get right to the point. Don’t make the other person sit through an excruciating 15 minutes of small talk about today’s weather or last night’s company softball game. And make sure your point is clear; don’t bury the lead, as they say in the journalism business. Think through what the information you’re giving means to the person or people you’re sharing it with and do them the courtesy of communicating that meaning clearly. For example, if you make a key management hire without involving some of their future reports, don’t just announce the new position, but also help the team understand who they are going to be reporting to and reassure them that no one is losing their jobs.

Stay focused.

Flexibility is one thing. Losing control of the conversation is another. Yes, it’s important to listen to the other person and respond to what they’re saying in the moment, but it’s also important not to get completely sidetracked by what you’re hearing. Be ready for what one trainer calls “deflections” – as when someone tries to change the subject, or wants to make the conversation about you instead of about the issue, or becomes overwrought to the point where it’s more about how they’re feeling than about what’s happening. This is especially important in situations where you’re dealing with a topic that has the potential to become emotionally charged. If you have to talk to someone about bad behavior at the office, for example, what are you going to do if they start crying or shouting? Remember, you’ll never reach whatever positive goal you’ve set if you allow someone to let you forget what it is halfway through the conversation.

Know yourself.

It really helps to know what you’re bringing to the conversation – both the good and the bad. I mentioned earlier that I’m a positive person, and I’ve learned to understand what effect that has when I need to have a difficult conversation with someone. Think about your own personality traits and the impact they can have. Do you tend to be conflict-avoidant, for example? Or is it the opposite – do you tend to be confrontational? Are you someone who finds it easy to remain calm and rational even if a conversation threatens to become heated? Try to identify the qualities that will work in your favor as well as those that could sabotage your efforts. Work on a strategy for using the former to your advantage and doing what you can to minimize the latter.

No matter how long you’re in a leadership role, difficult conversations will to some degree always be just that – difficult. You may not get to the point where you to look forward to them, but I think if you remember the things you can do to keep them positive and productive, you’ll be able to look forward to the end results.

As the great-grandson of the Mexican general who shot off Pancho Villa’s leg, H.O. embodies the spirit of a true revolutionary. His infectious passion and uncanny ability to predict the future has led him to found many successful start-ups including: Flightlock (acquired by Control Risks), Finetooth (now called Mumboe), and one of the first online non-profit media organizations, the Texas Tribune. He leads the Umbel team with one eye focused on battle tactics, one eye focused on long-term vision, and one eye focused on his iPhone. H.O. studied electrical and biomechanical engineering at the University of Texas at Austin.